EP0119386A1 - Procédé d'obtention de D,L-homocystine (II) - Google Patents
Procédé d'obtention de D,L-homocystine (II) Download PDFInfo
- Publication number
- EP0119386A1 EP0119386A1 EP84100180A EP84100180A EP0119386A1 EP 0119386 A1 EP0119386 A1 EP 0119386A1 EP 84100180 A EP84100180 A EP 84100180A EP 84100180 A EP84100180 A EP 84100180A EP 0119386 A1 EP0119386 A1 EP 0119386A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- homocysteine
- disodium salt
- homocystine
- homocystin
- ions
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- ZTVZLYBCZNMWCF-UHFFFAOYSA-N homocystine Chemical compound [O-]C(=O)C([NH3+])CCSSCCC([NH3+])C([O-])=O ZTVZLYBCZNMWCF-UHFFFAOYSA-N 0.000 title claims abstract description 18
- 238000000034 method Methods 0.000 title claims description 5
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims abstract description 14
- FFFHZYDWPBMWHY-UHFFFAOYSA-N HOMOCYSTEINE Chemical compound OC(=O)C(N)CCS FFFHZYDWPBMWHY-UHFFFAOYSA-N 0.000 claims abstract description 14
- 238000003756 stirring Methods 0.000 claims abstract description 6
- 239000007864 aqueous solution Substances 0.000 claims abstract description 5
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims abstract description 4
- 230000003197 catalytic effect Effects 0.000 claims abstract description 4
- 229910001882 dioxygen Inorganic materials 0.000 claims abstract description 4
- 238000007254 oxidation reaction Methods 0.000 claims description 6
- 150000002500 ions Chemical class 0.000 claims description 5
- 230000003647 oxidation Effects 0.000 claims description 5
- 229910001385 heavy metal Inorganic materials 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- -1 iron(III) ions Chemical class 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- FFEARJCKVFRZRR-UHFFFAOYSA-N methionine Chemical compound CSCCC(N)C(O)=O FFEARJCKVFRZRR-UHFFFAOYSA-N 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- 230000017858 demethylation Effects 0.000 description 2
- 238000010520 demethylation reaction Methods 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000001335 demethylating effect Effects 0.000 description 1
- 150000002019 disulfides Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- RUTXIHLAWFEWGM-UHFFFAOYSA-H iron(3+) sulfate Chemical compound [Fe+3].[Fe+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O RUTXIHLAWFEWGM-UHFFFAOYSA-H 0.000 description 1
- 229910000360 iron(III) sulfate Inorganic materials 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/02—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of thiols
- C07C319/12—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of thiols by reactions not involving the formation of mercapto groups
Definitions
- the invention relates to a process for the production of D, L-homocystine by oxidation of the disodium salt of D, L-homocysteine.
- the initial pH is preferably adjusted to a value between 7.0 and 8.0 using an aqueous mineral acid, preferably hydrochloric acid.
- the pH of the reaction mixture is adjusted to about 5.3, advantageously with an aqueous mineral acid, preferably hydrochloric acid. It is advantageous if the pH is adjusted at an elevated temperature, for example 50 ° C., and the reaction mixture is then slowly cooled to room temperature with stirring, for example over the course of an hour.
- the D, L-homocystin is obtained when the stirring speed during the precipitation is measured so that the D, L-homocystin is just kept in suspension. It can then be separated particularly easily by filtration or centrifugation.
- the precipitated D, L-homocystin is filtered off, washed with 100 ml of water at 80 ° C and dried in a vacuum drying cabinet to constant weight.
- the yield of D, L-homocystin is 9.2 g, corresponding to 88% of theory.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AT84100180T ATE16279T1 (de) | 1983-03-18 | 1984-01-10 | Verfahren zur gewinnung von d,l-homocystin. |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE3309762 | 1983-03-18 | ||
DE3309762A DE3309762C1 (de) | 1983-03-18 | 1983-03-18 | Verfahren zur Herstellung von D,L-Homocystin (II) |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0119386A1 true EP0119386A1 (fr) | 1984-09-26 |
EP0119386B1 EP0119386B1 (fr) | 1985-10-30 |
Family
ID=6193873
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP84100180A Expired EP0119386B1 (fr) | 1983-03-18 | 1984-01-10 | Procédé d'obtention de D,L-homocystine (II) |
Country Status (6)
Country | Link |
---|---|
US (1) | US4550200A (fr) |
EP (1) | EP0119386B1 (fr) |
JP (1) | JPS59176249A (fr) |
AT (1) | ATE16279T1 (fr) |
CA (1) | CA1223887A (fr) |
DE (1) | DE3309762C1 (fr) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP3620221B2 (ja) * | 1996-11-25 | 2005-02-16 | 三菱化学株式会社 | ホモシスチンの製造法 |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2406362A (en) * | 1943-11-11 | 1946-08-27 | Du Pont | Process |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB621915A (en) * | 1945-12-20 | 1949-04-22 | Merck & Co Inc | Process of preparing penicillamine disulphides |
US3565959A (en) * | 1968-05-24 | 1971-02-23 | Nippon Oil Co Ltd | Process for oxidizing mercaptans to disulfides |
US3978137A (en) * | 1975-03-14 | 1976-08-31 | Universal Oil Products Company | Oxidation of sulfur-containing compounds |
-
1983
- 1983-03-18 DE DE3309762A patent/DE3309762C1/de not_active Expired
-
1984
- 1984-01-10 EP EP84100180A patent/EP0119386B1/fr not_active Expired
- 1984-01-10 AT AT84100180T patent/ATE16279T1/de active
- 1984-03-15 US US06/590,059 patent/US4550200A/en not_active Expired - Fee Related
- 1984-03-16 CA CA000449825A patent/CA1223887A/fr not_active Expired
- 1984-03-16 JP JP59049427A patent/JPS59176249A/ja active Granted
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2406362A (en) * | 1943-11-11 | 1946-08-27 | Du Pont | Process |
Non-Patent Citations (1)
Title |
---|
CHEMICAL ABSTRACTS, Band 70, Nr. 19, 12. Mai 1969, Seite 13, Nr. 84330p, Columbus, Ohio, USA; D. CAVALLINI et al.: "Copper-catalyzed oxidation of cysteine to cystine" & ARCH. BIOCHEM. BIOPHYS. 1969, 130(1), 354-361 * |
Also Published As
Publication number | Publication date |
---|---|
EP0119386B1 (fr) | 1985-10-30 |
ATE16279T1 (de) | 1985-11-15 |
JPS59176249A (ja) | 1984-10-05 |
CA1223887A (fr) | 1987-07-07 |
DE3309762C1 (de) | 1984-03-01 |
US4550200A (en) | 1985-10-29 |
JPH0417189B2 (fr) | 1992-03-25 |
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